Will Smith received a lesson in stand-up comedy from Dave Chappelle for his new Facebook Watch show, Will Smith’s Bucket List. But Smith’s stand-up experience is a life lesson for us all. When Smith celebrated his 50th birthday, he decided to tackle his bucket list in a series of episodes on Facebook Watch. His first episodes follow the Aladdin star as he skydives and swims with sharks—it has the potential to be just fluff.

However, in this new episode, Smith has just one week to prepare a stand-up routine with Chappelle’s help. Confronting fears and finding meaningful connections could prepare one for their first open mic or the struggles of day-to-day life.

As Smith mentally prepares, he admits that performing stand-up is even more intimidating than his upcoming bucket list item of bungee jumping from a helicopter over the Grand Canyon. “There’s nothing in entertainment that is more terrifying to me than standing up in front of an audience with just a microphone with the anticipation that you will make people laugh. Yet when you connect to people, there’s nothing like that.”

Will Smith tries stand-up comedy on Bucket List

The former Fresh Prince of Bel-Air seems to realize the true skill required to perform stand-up well and does not assume that his fame and acting chops will get him by—unlike other comedic actors flippantly tossing their hats into the stand-up game. While some comics would complain that the last thing LA needs is yet another actor trying to perform stand-up, Chappelle sees Smith as someone people can root for. Chappelle admits that “being a good dude in comedy, that’s rare. Comics are assholes.”

Chappelle offers three pieces of advice for Smith, but the lessons go beyond the stage. 1. Confidence is key. 2. Pick the right shit to talk about. 3. Be interesting all the time.

Dave Chappelle: “If they can feel you, they will never forget you.”

Chappelle adds, “If they can feel you, they will never forget you.” The two-time Grammy-winner comments on the fun and importance of being “self-aware in front of people.” The mentor and student connect with friends, such as Alfonso Ribeiro who co-starred with Smith on Fresh Prince and Neal Brennan who co-created Chappelle’s Show, to help structure a meaningful routine.

As Smith performs to a surprised crowd of friends and family at the Peppermint Room in LA, he truly starts to open up. He stops pacing and looking down and starts to calm down and embrace the crowd with typical first-timer material about his family.

At 50, Smith may or may not be experiencing a stunningly standard midlife crisis. The Bad Boys star says he wants to live life for himself. Admittedly addicted to adoration, Smith seems to have realized that it’s important to step out of your comfort zone even if it leads to embarrassment and failure.

On this new episode of Will Smith’s Bucket List, Chappelle helps the actor discover the magic of stand-up comedy: using negative emotions and turn them into laughter.

Watch the 22-minute long episode below and like Will Smith’s Bucket List on Facebook Watch.

Mary Stevens

Mary Stevens is a stand-up comedy enthusiast. She is a huge fan of live stand-up comedy and produces a show in her backyard in Hermosa Beach, CA. Her show has featured comics from Netflix, Comedy Central, HBO, Showtime and SNL, as well as up-and-coming comics. She is active on Twitter and Instagram @hermosabchmary.